| 2020-12-12 | ChesterfieldvBarnetNational League · England | 6–0 | National League · England |
| 2020-12-08 | SuttonvChesterfieldNational League · England | 0–1 | National League · England |
| 2020-12-01 | ChesterfieldvAldershotNational League · England | 0–0 | National League · England |
| 2020-11-28 | WeymouthvChesterfieldNational League · England | 1–2 | National League · England |
| 2020-11-21 | ChesterfieldvNotts CountyNational League · England | 2–3 | National League · England |
| 2020-11-17 | AltrinchamvChesterfieldNational League · England | 3–2 | National League · England |
| 2020-11-14 | ChesterfieldvMaidenheadNational League · England | 1–2 | National League · England |
| 2020-10-31 | YeovilvChesterfieldNational League · England | 0–1 | National League · England |
| 2020-10-20 | WealdstonevChesterfieldNational League · England | 3–2 | National League · England |
| 2020-10-17 | ChesterfieldvStockportNational League · England | 1–2 | National League · England |
| 2020-10-13 | TorquayvChesterfieldNational League · England | 2–1 | National League · England |
| 2020-10-10 | ChesterfieldvWokingNational League · England | 4–0 | National League · England |
| 2020-10-06 | ChesterfieldvHartlepoolNational League · England | 1–2 | National League · England |
| 2020-03-14 | Dover AthleticvChesterfieldNational League · England | 1–1 | National League · England |
| 2020-03-07 | ChorleyvChesterfieldNational League · England | 1–2 | National League · England |
| 2020-03-03 | ChesterfieldvHarrogateNational League · England | 3–4 | National League · England |
| 2020-02-22 | ChesterfieldvEbbsfleetNational League · England | 4–0 | National League · England |
| 2020-02-08 | ChesterfieldvWrexhamNational League · England | 3–2 | National League · England |
| 2020-02-01 | Notts CountyvChesterfieldNational League · England | 3–0 | National League · England |
| 2020-01-25 | ChesterfieldvFyldeNational League · England | 1–1 | National League · England |
| 2020-01-18 | EastleighvChesterfieldNational League · England | 0–2 | National League · England |
| 2020-01-04 | ChesterfieldvSuttonNational League · England | 1–0 | National League · England |
| 2020-01-01 | SolihullvChesterfieldNational League · England | 3–0 | National League · England |